Why do nullable bools not allow if(nullable) but do allow if(nullable == true)?

There's no implicit conversion from Nullable<bool> to bool. There is an implicit conversion from bool to Nullable<bool> and that's what happens (in language terms) to each of the bool constants in the first version. The bool operator==(Nullable<bool>, Nullable<bool> operator is then applied. (This isn't quite the same as other lifted operators - the result is just bool, not Nullable<bool>.)

In other words, the expression 'fred == false' is of type bool, whereas the expression 'fred' is of type Nullable<bool> hence you can't use it as the "if" expression.

EDIT: To answer the comments, there's never an implicit conversion from Nullable<T> to T and for good reason - implicit conversions shouldn't throw exceptions, and unless you want null to be implicitly converted to default(T) there's not a lot else that could be done.

Also, if there were implicit conversions both ways round, an expression like "nullable + nonNullable" would be very confusing (for types that support +, like int). Both +(T?, T?) and +(T, T) would be available, depending on which operand were converted - but the results could be very different!

I'm 100% behind the decision to only have an explicit conversion from Nullable<T> to T.

Because fred is not a boolean. it is a struct, which has a boolean property called IsNull, or HasValue, or whatever... The object named fred is the complex composite object containing a boolean and a value, not a primitive boolean itself...

Below, for example is how a Nullable Int could be implemented. The generic Nullable is almost certainly implemented similarly (but generically). You can see here how the implicit and explicit conversions are implemented..

public struct DBInt
   {
       // The Null member represents an unknown DBInt value.
       public static readonly DBInt Null = new DBInt();
       // When the defined field is true, this DBInt represents a known value
       // which is stored in the value field. When the defined field is false,
       // this DBInt represents an unknown value, and the value field is 0.
       int value;
       bool defined;
       // Private instance constructor. Creates a DBInt with a known value.
       DBInt(int value) 
       {
              this.value = value;
              this.defined = true;
       }
       // The IsNull property is true if this DBInt represents an unknown value.
       public bool IsNull { get { return !defined; } }
       // The Value property is the known value of this DBInt, or 0 if this
       // DBInt represents an unknown value.
       public int Value { get { return value; } }
       // Implicit conversion from int to DBInt.
       public static implicit operator DBInt(int x) 
       { return new DBInt(x); }

       // Explicit conversion from DBInt to int. Throws an exception if the
       // given DBInt represents an unknown value.
       public static explicit operator int(DBInt x) 
       {
              if (!x.defined) throw new InvalidOperationException();
              return x.value;
       }
       public static DBInt operator +(DBInt x) 
       { return x; }
       public static DBInt operator -(DBInt x) 
       { return x.defined? -x.value: Null; }
       public static DBInt operator +(DBInt x, DBInt y) 
       {
              return x.defined && y.defined? 
                      x.value + y.value: Null;
       }
       public static DBInt operator -(DBInt x, DBInt y) 
       {
              return x.defined && y.defined?  
                      x.value - y.value: Null;
       }
       public static DBInt operator *(DBInt x, DBInt y) 
       {
              return x.defined && y.defined?  
                      x.value * y.value: Null;
       }
       public static DBInt operator /(DBInt x, DBInt y) 
       {
              return x.defined && y.defined?  
                     x.value / y.value: Null;
       }
       public static DBInt operator %(DBInt x, DBInt y) 
       {
              return x.defined && y.defined?  
                      x.value % y.value: Null;
       }
       public static DBBool operator ==(DBInt x, DBInt y) 
       {
              return x.defined && y.defined?  
                     x.value == y.value: DBBool.Null;
       }
       public static DBBool operator !=(DBInt x, DBInt y) 
       {
              return x.defined && y.defined?  
                     x.value != y.value: DBBool.Null;
       }
       public static DBBool operator >(DBInt x, DBInt y) 
       {
              return x.defined && y.defined?  
                     x.value > y.value: DBBool.Null;
       }
       public static DBBool operator <(DBInt x, DBInt y) 
       {
              return x.defined && y.defined?  
                     x.value < y.value: DBBool.Null;
       }
       public static DBBool operator >=(DBInt x, DBInt y) 
       {
              return x.defined && y.defined?  
                      x.value >= y.value: DBBool.Null;
       }
       public static DBBool operator <=(DBInt x, DBInt y) 
       {
              return x.defined && y.defined?  
                     x.value <= y.value: DBBool.Null;
       }
       public override bool Equals(object o) 
       {
              try { return (bool) (this == (DBInt) o); } 
              catch  { return false; }
       }
       public override int GetHashCode() 
       { return (defined)? value: 0; }   
       public override string ToString() 
       { return (defined)? .ToString(): "DBInt.Null"; }   
   }

The statement Nullable<bool> == true is implicitly checking Nullable<bool> == (Nullable<bool>)true.

Note that Nullable<bool> itself is not a boolean. It is a wrapper for a boolean that can also be set to null.